1-carboxymethyl-9-xanthenone | 59292-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-carboxymethyl-9-xanthenone
• 英文别名: xanthone-1-acetic acid；(9-oxo-xanthen-1-yl)-acetic acid；(9-Oxo-xanthen-1-yl)-essigsaeure；9H-Xanthene-1-acetic acid, 9-oxo-；2-(9-oxoxanthen-1-yl)acetic acid
• CAS: 59292-04-5
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: RBRKQSDAFTVFQD-UHFFFAOYSA-N

物化性质

• 熔点：
  245 °C(Solv: 1,4-dioxane (123-91-1); water (7732-18-5))
• 沸点：
  502.7±39.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  cyanomethylxanthone 在 硫酸 、 水 、 溶剂黄146 作用下， 生成 1-carboxymethyl-9-xanthenone
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012

文献信息

• Oxidation of 9-Xanthenones with Lead(IV) Acetate. Formation of Di-γ-lactones
  作者：Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1246/bcsj.56.2847

  日期：1983.9

  The oxidation of 9-xanthenones with lead(IV) acetate afforded 3a,3b,6a,12b-tetrahydro-2H-difuro[3,2-a:3′,2′-c]xanthene-2,5,7(3H,6H)-triones in addition to other products. Characterization of the di-γ-lactones and the difference between the oxidation reaction of lead(IV) and manganese(III) acetates in the 9-xanthenone system are discussed.

  用乙酸铅 (IV) 氧化 9-呫吨酮得到 3a,3b,6a,12b-四氢-2H-二呋喃 [3,2-a:3',2'-c]xanthene-2,5,7(3H ,6H)-triones 以及其他产品。讨论了二-γ-内酯的表征以及 9-呫吨酮系统中乙酸铅 (IV) 和乙酸锰 (III) 的氧化反应之间的差异。
• [EN] POLY(ADP-RIBOSE) POLYMERASE ("PARP") INHIBITORS, METHODS AND PHARMACEUTICAL COMPOSITIONS FOR TREATING NEURAL OR CARDIOVASCULAR TISSUE DAMAGE<br/>[FR] INHIBITEUR DE LA POLY(ADP-RIBOSE) POLYMERASE (PARP), PROCEDES, ET COMPOSITIONS PHARMACEUTIQUES PERMETTANT DE TRAITER LES LESIONS DE TISSUS NERVEUX OU CARDIOVASCULAIRES
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：WO1999011645A1

  公开（公告）日：1999-03-11

  (EN) This invention relates to compounds, pharmaceutical compositions, and methods of using compounds of formula (I), or a pharmaceutically acceptable salt, hydrate, prodrug, or mixtures thereof, wherein: Y is alkylhalo, alkyl-CO-G, COG, a direct bond, C=O, O, NR11, or CR8; G is NR11R16, OR9, SR9, or R10; Z is O, S or NR11; X is NR16, O, S, CR12R13, C=O, a bond, -CR12=CR13-, -C(R12R13)C(R14R15)-, or R1, R2, R3, R4, R5, R6, R7, R8, R10, R12, R13, R14, or R15, are independently: hydrogen, halo, alkylhalo, hydroxy, C1-C9 straight or branched chain alkyl, C2-C9 straight or branched chain alkenyl group, C3-C8 cycloalkyl, C5-C7 cycloalkenyl, aryl, amino, alkylamino, nitro, nitroso, carboxy, or aralkyl; R9 is hydrogen, hydroxy, C1-C9 straight or branched chain alkyl, C2-C9 straight or branched chain alkenyl group, C3-C8 cycloalkyl, C5-C7 cycloalkenyl, aryl, amino, alkylamino, carboxy, or aralkyl; R11 or R16 are independently: hydrogen, halo, alkylhalo, hydroxy, C1-C9 straight or branched chain alkyl, C2-C9 straight or branched chain alkenyl group, C3-C8 cycloalkyl, C5-C7 cycloalkenyl, aryl, amino, alkylamino, carboxy, or aralkyl.(FR) L'invention concerne des composés, des compositions pharmaceutiques, et des procédés d'utilisation de ces composés, de formule (I) ou un sel, un hydrate, un promédicament, ou des mélanges pharmaceutiquement acceptables de ceux-ci, Y représentant alkyhalo, alkyl-CO-G-, COG, une liaison directe, C=O, O, NR11, ou CR8; G représentant NR11R16, OR9, SR9, ou R10; Z représentant O, S, ou NR11; X représentant NR16, O, S, CR12R13, C=O, une liaison, -CR12=CR13-, -C(R12R13)C(R14R15)-, ou; R1, R2, R3, R4, R5, R6, R7, R8, R10, R12, R13, R14, ou R15, représentant indépendamment: hydrogène, halo, alkylhalo, hydroxy, un alkyle en C1-C9 à chaîne linéaire ou ramifiée, un groupe alkényle en C2-C9 à chaîne linéaire ou ramifiée, un cycloalkyle en C3-C8, un cycloalkényle en C5-C7, un aryle, un amino, un alkylamino, un nitro, un nitroso, un carboxy, ou un aralkyle; R9 représentant indépendamment un hydrogène, un hydroxy, un alkyle en C1-C9 à chaîne linéaire ou ramifiée, un groupe alkényle en C2-C9 à chaîne linéaire ou ramifiée, un cycloalkyle en C3-C8, un cycloalkényle en C5-C7, un aryle, un amino, un alkylamino, un carboxy, ou un aralkyle; R11 ou R16 représentant indépendamment: un hydrogène, un halo, un alkylhalo, un hydroxy, un alkyle en C1-C9 à chaîne linéaire ou ramifiée, un groupe alkényle en C2-C9 à chaîne linéaire ou ramifiée, un cycloalkyle en C3-C8, un cycloalkényle en C5-C7, un aryle, un amino, un alkylamino, un carboxy, ou un aralkyle.

  （中文）本发明涉及一种化合物、药物组合物和使用化合物的方法，其公式为（I）或其药学上可接受的盐、水合物、前药或其混合物，其中：Y是烷基卤素、烷基-CO-G、COG、直接键、C=O、O、NR11或CR8; G是NR11R16、OR9、SR9或R10; Z是O、S或NR11; X是NR16、O、S、CR12R13、C=O、键、-CR12=CR13-、-C(R12R13)C(R14R15)-或R1、R2、R3、R4、R5、R6、R7、R8、R10、R12、R13、R14或R15，独立地表示：氢、卤素、烷基卤素、羟基、C1-C9直链或支链烷基、C2-C9直链或支链烯基基团、C3-C8环烷基、C5-C7环烯基、芳基、氨基、烷基氨基、硝基、亚硝基、羧基或芳基烷基；R9独立地表示：氢、羟基、C1-C9直链或支链烷基、C2-C9直链或支链烯基基团、C3-C8环烷基、C5-C7环烯基、芳基、氨基、烷基氨基、羧基或芳基烷基；R11或R16独立地表示：氢、卤素、烷基卤素、羟基、C1-C9直链或支链烷基、C2-C9直链或支链烯基基团、C3-C8环烷基、C5-C7环烯基、芳基、氨基、烷基氨基、羧基或芳基烷基。
• Kruber, Chemische Berichte, 1937, vol. 70, p. 1556,1563
  作者：Kruber

  DOI：——

  日期：——
• Compounds having antitumour and antibacterial properties
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0278176B1

  公开（公告）日：1994-03-09
• NAKANISHI MICHIO; OE TAKANORI; TSURUDA MINEO; MATSUO HIROSHI; SAKURAGI SH+, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. <YKKZ-AJ>, 1976, 96+
  作者：NAKANISHI MICHIO、 OE TAKANORI、 TSURUDA MINEO、 MATSUO HIROSHI、 SAKURAGI SH+

  DOI：——

  日期：——